Exploration of allosteric agonism structure-activity relationships within an acetylene series of metabotropic glutamate receptor 5 (mGlu5) positive allosteric modulators (PAMs): discovery of 5-((3-fluorophenyl)ethynyl)-N-(3-methyloxetan-3-yl)picolinamide (ML254)

J Med Chem. 2013 Oct 24;56(20):7976-96. doi: 10.1021/jm401028t. Epub 2013 Oct 9.

Abstract

Positive allosteric modulators (PAMs) of metabotropic glutamate receptor 5 (mGlu5) represent a promising therapeutic strategy for the treatment of schizophrenia. Both allosteric agonism and high glutamate fold-shift have been implicated in the neurotoxic profile of some mGlu5 PAMs; however, these hypotheses remain to be adequately addressed. To develop tool compounds to probe these hypotheses, the structure-activity relationship of allosteric agonism was examined within an acetylenic series of mGlu5 PAMs exhibiting allosteric agonism in addition to positive allosteric modulation (ago-PAMs). PAM 38t, a low glutamate fold-shift allosteric ligand (maximum fold-shift ~ 3.0), was selected as a potent PAM with no agonism in the in vitro system used for compound characterization and in two native electrophysiological systems using rat hippocampal slices. PAM 38t (ML254) will be useful to probe the relative contribution of cooperativity and allosteric agonism to the adverse effect liability and neurotoxicity associated with this class of mGlu5 PAMs.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylene / chemical synthesis
  • Acetylene / chemistry
  • Acetylene / pharmacology*
  • Allosteric Regulation / drug effects
  • Amides / chemical synthesis
  • Amides / chemistry
  • Amides / pharmacology
  • Animals
  • Binding, Competitive
  • Cell Membrane / metabolism
  • Drug Discovery / methods
  • Excitatory Postsynaptic Potentials / drug effects
  • HEK293 Cells
  • Hippocampus / drug effects
  • Hippocampus / physiology
  • Humans
  • Male
  • Models, Chemical
  • Models, Molecular
  • Molecular Structure
  • Picolinic Acids / chemical synthesis
  • Picolinic Acids / chemistry
  • Picolinic Acids / pharmacology*
  • Protein Structure, Tertiary
  • Radioligand Assay
  • Rats
  • Rats, Sprague-Dawley
  • Receptor, Metabotropic Glutamate 5 / agonists*
  • Receptor, Metabotropic Glutamate 5 / chemistry
  • Receptor, Metabotropic Glutamate 5 / metabolism
  • Structure-Activity Relationship

Substances

  • 5-((3-fluorophenyl)ethynyl)-N-(3-methyloxetan-3-yl)picolinamide
  • Amides
  • Picolinic Acids
  • Receptor, Metabotropic Glutamate 5
  • picolinamide
  • Acetylene